Trimethylamine → HCID 69898250, compound

HRID 2308201Notes

Reaction equation

HRID 2308201 reaction equation
CN(C)C.[CH3:5][O:6][CH2:7][CH:8]1[O:29][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[O:10][CH:9]1[CH2:30][O:31][CH3:32])[N:18]=[CH:17][N:16]=[C:15]3[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24](I)[CH:23]=1.[CH3:33][Si:34]([CH3:38])([CH3:37])[C:35]#[CH:36]>[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:5][O:6][CH2:7][CH:8]1[O:29][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[O:10][CH:9]1[CH2:30][O:31][CH3:32])[N:18]=[CH:17][N:16]=[C:15]3[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:36]#[C:35][Si:34]([CH3:38])([CH3:37])[CH3:33])[CH:23]=1

Participants

6

Reactant 3

HCID 1146TrimethylamineHCID 66111TrimethylsilylacetyleneHCID 20747428HCID 20747428, compound

Product 1

HCID 69898250HCID 69898250, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

3 ml of trimethylamine was mixed with the titled compound of Example 45 (40 mg, 0.075 mmol), 1-trimethylsilylacetylene (15 mg, 0.15 mmol), copper iodide (16 mg, 0.084 mmol) and tetrakis(triphenylphosphine)palladium (26 mg, 0.022 mmol), followed by stirring for 12 hours at a room temperature. Then, the reaction mixture was filtered to obtain a filtrate, which was then concentrated and purified by a column chromatography (mobile phase: hexane:ethylacetate=2:3(v:v)) to prepare the titled compound (33 mg, 97%).

Workup

  1. filtrationThen, the reaction mixture was filtered
  2. customto obtain a filtrate, which
  3. concentrationwas then concentrated
  4. custompurified by a column chromatography (mobile phase: hexane:ethylacetate=2:3(v:v))
  5. customto prepare the titled compound (33 mg, 97%)

Sources & evidence

ORD record
ord-f8b653e923424b76aaddd824c8f88c6a
Source dataset
uspto-grants-2004_12
Patent number
US06835735B2

Reaction notes

Loading…